Planning a Prison Break: Lifehack 101

Planning a Prison Break is an art. No wait, it’s a science. Okay, it’s more of an artsy-science that requires equal parts planning, daring, luck, stupidity and guts. (With the “guts” part hopefully remaining on the interior)

But at the root of all prison breaks is the burning desire for one thing: Freedom. (A desire that I know well) And truthfully, many of the elements of a successful prison break can be applied to almost any life-changing event. Would you like your life to be different? If you answered “yes” to this question, then you need a Lifehack. And you need a Plan. What do you want? When do you want it? And how are you going to make this happen?

I’ve watched a lot of prison break movies, so I’m basically an expert at this point. Here’s what I’ve learned thus far:

  • Picking your team is paramount.

 True, there have been some ballsy, successful solo prison breaks, but for the most part, prison breaks are a team effort. So choose your team wisely. I’m very lucky to have people* in my corner who support me, cheer me on and tell me on a regular basis “You can do this thing!”

(*You people know who you are….and I totally, completely, thoroughly LOVE YOU!!!)

  • Devise your Cunning Plan

 (This is the part where you lay out all the hand-drawn maps. I love this part.) What is your oh-so-brilliant plan to blow this popsicle stand? What are your weaknesses? What are your strengths? What cock-eyed ideas have you figured out to get from point A to point B? And remember, some of the best prison breaks of all time have relied on some very wild, insane, or completely mad ideas….and worked. Just because it’s totally nuts, doesn’t mean it won’t work. Your job is to make it work.

  • Expect the Unexpected

No plan goes entirely to plan. That’s why you need to plan for the eventuality of Things Going Terribly Wrong. What are you going to do if you accidentally tunneled inside the walls? What are you going to do if the getaway car is a donkey cart? Identify all of these potential pitfalls and figure out a patch. (Hint: Donkeys can be made to go faster and they can go off-road.) 

  • Plan for Redundancy

 Don’t put all your eggs in one basket. (Someone here said, “No one can eat fifty eggs” from Cool Hand Luke didn’t you? You can admit it.) If you hinge your entire escape plan on one thing, and that one thing fails, you’re going back to prison. So diversify. What’s your backup plan if the guard doesn’t get drunk, or the key you made out of a bar of soap melts, or the donkey only has three legs?

  • Do the Work

This is possibly the most important step. (Well, after having a brilliantly cunning plan.) Once you know what you have to do and when, DO IT! Put in the time. Do the work. Check off your lists. Drink lots of coffee. Do MORE WORK. Make it happen. Having the most brilliant prison break plan in the history of the brilliant prison break plans is totally useless if you never implement it.

And remember, if your prison break fails, you’re probably going back to prison. So really you wouldn’t be that far off from where you started. (Maybe with a sliiightly longer sentence.) But really, compared to just staying in prison, what’s to stop you from going for the Big Goal.

Say it with me now: “What do we want? Freedom. When do we want it? Forever!”


  1. And if you do get caught, you'll get more time to plan the next one!

    1. Haha! Probably a A LOT more time!! As in, 15 to 20 years. I'm cool with it though, better than sitting here waiting for a shiv in the kidneys. :)

  2. I'm so in.

    I've got some gum, a shoelace or two, dental floss, and a few other key MacGyver-esque gadgets at the ready...

    And if for some dumb stroke of luck we get caught (which is totally NOT gonna happen), I'm pretty apt at whistling the "Bridge Over River Kwai" theme song.

    We've so got this.

    1. 1. *dies laughing*
      2. I Love you SO MUCH!!!
      3. Get your MacGyver gadgets ready....standby.
      4. I would LOVE to hear you whistle the Bridge of the River Kwai theme song. We must make this happen. :)